Transporter studies with the 3-O-sulfate conjugate of 17α- ethinylestradiol: Assessment of human kidney drug transporters

Drug Metabolism and Disposition

Volumn 38, Issue 7, 2010, Pages 1064-1071

  Han, Yong Hae ^a   Busler, Dennis ^a   Hong, Yang ^a   Tian, Yuan ^a   Chen, Cliff ^a   Rodrigues, A David ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

17ALPHA ETHINYLESTRADIOL 3 O SULFATE; BROMSULFOPHTHALEIN; CARRIER PROTEIN; CIMETIDINE; DRUG METABOLITE; ETHINYLESTRADIOL; METHOTREXATE; MULTIDRUG AND TOXIN EXTRUSION 1; MULTIDRUG RESISTANCE PROTEIN 4; ORGANIC ANION TRANSPORTER 1; ORGANIC ANION TRANSPORTER 3; ORGANIC ANION TRANSPORTER 4; ORGANIC CATION TRANSPORTER 2; PROBENECID; UNCLASSIFIED DRUG; ABC TRANSPORTER; ABCB11 PROTEIN, HUMAN; ABCG2 PROTEIN, HUMAN; COTRANSPORTER; ETHINYLESTRADIOL-3-SULFATE; MULTIDRUG RESISTANCE PROTEIN; ORGANIC ANION TRANSPORTER; SLCO1B1 PROTEIN, HUMAN; SLCO2B1 PROTEIN, HUMAN; SODIUM-BILE ACID COTRANSPORTER; TUMOR PROTEIN;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG UPTAKE; EMBRYO; EPITHELIUM CELL; HUMAN; HUMAN CELL; INSECT CELL; KIDNEY CELL; KIDNEY EPITHELIUM; KIDNEY PROXIMAL TUBULE; KIDNEY TUBULE EPITHELIUM; MEMBRANE VESICLE; MICHAELIS CONSTANT; NONHUMAN; PHENOTYPE; PRIORITY JOURNAL; URINARY EXCRETION; ACTIVE TRANSPORT; ANALOGS AND DERIVATIVES; BIOSYNTHESIS; DRUG EFFECTS; GENETIC TRANSFECTION; GENETICS; KINETICS; LIVER; LIVER CELL; METABOLISM; PROCEDURES; TRANSFORMED CELL LINE;

HEXAPODA;

ATP-BINDING CASSETTE TRANSPORTERS; BIOLOGICAL TRANSPORT, ACTIVE; CARRIER PROTEINS; CELL LINE, TRANSFORMED; ETHINYL ESTRADIOL; HEPATOCYTES; HUMANS; KINETICS; LIVER; MULTIDRUG RESISTANCE-ASSOCIATED PROTEINS; NEOPLASM PROTEINS; ORGANIC ANION TRANSPORTERS; ORGANIC ANION TRANSPORTERS, SODIUM-DEPENDENT; P-GLYCOPROTEIN; SYMPORTERS; TRANSFECTION;

EID: 77953758519     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.109.031526     Document Type: Article

References (36)

1. Aslamkhan A, Han YH, Walden R, Sweet DH, and Pritchard JB (2003) Stoichiometry of organic anion/dicarboxylate exchange in membrane vesicles from rat renal cortex and hOAT1-expressing cells. Am J Physiol Renal Physiol 285:F775-F783.
2. Babu E, Takeda M, Narikawa S, Kobayashi Y, Enomoto A, Tojo A, Cha SH, Sekine T, Sakthisekaran D, and Endou H (2002) Role of human organic anion transporter 4 in the transport of ochratoxin A. Biochim Biophys Acta 1590:64-75. (Pubitemid 34626769)
3. Back DJ, Bolt HM, Breckenridge AM, Crawford FE, Orme ML, Rowe PH, and Schindler AE (1980) The pharmacokinetics of a large (3 mg) oral dose of ethynylestradiol in women. Contraception 21:145-153. (Pubitemid 10112997)
4. Brown CD, Sayer R, Windass AS, Haslam IS, De Broe ME, D'Haese PC, and Verhulst A (2008) Characterisation of human tubular cell monolayers as a model of proximal tubular xenobiotic handling. Toxicol Appl Pharmacol 233:428-438.
5. Cha SH, Sekine T, Fukushima JI, Kanai Y, Kobayashi Y, Goya T, and Endou H (2001) Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. Mol Pharmacol 59:1277-1286. (Pubitemid 32385197)
6. Cha SH, Sekine T, Kusuhara H, Yu E, Kim JY, Kim DK, Sugiyama Y, Kanai Y, and Endou H (2000) Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta. J Biol Chem 275:4507-4512.
7. Chen ZS, Lee K, Walther S, Raftogianis RB, Kuwano M, Zeng H, and Kruh GD (2002) Analysis of methotrexate and folate transport by multidrug resistance protein 4 (ABCC4): MRP4 is a component of the methotrexate efflux system. Cancer Res 62:3144-3150.
8. Chen ZS, Robey RW, Belinsky MG, Shchaveleva I, Ren XQ, Sugimoto Y, Ross DD, Bates SE, and Kruh GD (2003) Transport of methotrexate, methotrexate polyglutamates, and 17betaestradiol 17-(beta-D-glucuronide) by ABCG2: effects of acquired mutations at R482 on methotrexate transport. Cancer Res 63:4048-4054.
9. Chu XY, Huskey SE, Braun MP, Sarkadi B, Evans DC, and Evers R (2004) Transport of ethinylestradiol glucuronide and ethinylestradiol sulfate by the multidrug resistance proteins MRP1, MRP2, and MRP3. J Pharmacol Exp Ther 309:156-164.
10. Cusatis G and Sparreboom A (2008) Pharmacogenomic importance of ABCG2. Pharmacogenomics 9:1005-1009.
11. Deguchi T, Kusuhara H, Takadate A, Endou H, Otagiri M, and Sugiyama Y (2004) Characterization of uremic toxin transport by organic anion transporters in the kidney. Kidney Int 65:162-174.
12. Ekaratanawong S, Anzai N, Jutabha P, Miyazaki H, Noshiro R, Takeda M, Kanai Y, Sophasan S, and Endou H (2004) Human organic anion transporter 4 is a renal apical organic anion/dicarboxylate exchanger in the proximal tubules. J Pharmacol Sci 94:297-304.
13. Han YH, Busler D, Hong Y, Tian Y, Chen C, and Rodrigues AD (2010) Transporter studies with the 3-O-sulfate conjugate of 17α- ethinylestradiol: assessment of human liver drug transporters. Drug Metab Dispos 38:1072-1082.
14. Ito S, Kusuhara H, Kuroiwa Y, Wu C, Moriyama Y, Inoue K, Kondo T, Yuasa H, Nakayama H, Horita S, et al. (2009) Potent and specific inhibition of mMate1-mediated efflux of type I organic cations in the liver and kidney by pyrimethamine. J Pharmacol Exp Ther 333:341-350.
15. Kimura H, Takeda M, Narikawa S, Enomoto A, Ichida K, and Endou H (2002) Human organic anion transporters and human organic cation transporters mediate renal transport of prostaglandins. J Pharmacol Exp Ther 301:293-298. (Pubitemid 34250307)
16. Lee W and Kim RB (2004) Transporters and renal drug elimination. Annu Rev Pharmacol Toxicol 44:137-166.
17. Li AP, Hartman NR, Lu C, Collins JM, and Strong JM (1999) Effects of cytochrome P450 inducers on 17alpha-ethinyloestradiol (EE2) conjugation by primary human hepatocytes. Br J Clin Pharmacol 48:733-742.
18. Maeda K and Sugiyama Y (2008) Impact of genetic polymorphisms of transporters on the pharmacokinetic, pharmacodynamic and toxicological properties of anionic drugs. Drug Metab Pharmacokinet 23:223-235.
19. Maggs JL, Grimmer SF, Orme ML, Breckenridge AM, Park BK, and Gilmore IT (1983) The biliary and urinary metabolites of [3H]17 alpha-ethynylestradiol in women. Xenobiotica 13:421-431. (Pubitemid 13023098)
20. Mikkaichi T, Suzuki T, Onogawa T, Tanemoto M, Mizutamari H, Okada M, Chaki T, Masuda S, Tokui T, Eto N, et al. (2004) Isolation and characterization of a digoxin transporter and its rat homologue expressed in the kidney. Proc Natl Acad Sci USA 101:3569-3574.
21. Nakatomi K, Yoshikawa M, Oka M, Ikegami Y, Hayasaka S, Sano K, Shiozawa K, Kawabata S, Soda H, Ishikawa T, et al. (2001) Transport of 7-ethyl-10-hydroxycamptothecin (SN-38) by breast cancer resistance protein ABCG2 in human lung cancer cells. Biochem Biophys Res Commun 288:827-832.
22. Nozaki Y, Kusuhara H, Kondo T, Hasegawa M, Shiroyanagi Y, Nakazawa H, Okano T, and Sugiyama Y (2007) Characterization of the uptake of organic anion transporter (OAT) 1 and OAT3 substrates by human kidney slices. J Pharmacol Exp Ther 321:362-369.
23. Robertson EE and Rankin GO (2006) Human renal organic anion transporters: characteristics and contributions to drug and drug metabolite excretion. Pharmacol Ther 109:399-412.
24. Schrag ML, Cui D, Rushmore TH, Shou M, Ma B, and Rodrigues AD (2004) Sulfotransferase 1E1 is a low km isoform mediating the 3-O-sulfation of ethinyl estradiol. Drug Metab Dispos 32:1299-1303.
25. Suzuki M, Suzuki H, Sugimoto Y, and Sugiyama Y (2003) ABCG2 transports sulfated conjugates of steroids and xenobiotics. J Biol Chem 278:22644-22649.
26. Sweet DH, Miller DS, Pritchard JB, Fujiwara Y, Beier DR, and Nigam SK (2002) Impaired organic anion transport in kidney and choroid plexus of organic anion transporter 3 (Oat3 (Slc22a8)) knockout mice. J Biol Chem 277:26934-26943.
27. Tahara H, Kusuhara H, Endou H, Koepsell H, Imaoka T, Fuse E, and Sugiyama Y (2005) A species difference in the transport activities of H2 receptor antagonists by rat and human renal organic anion and cation transporters. J Pharmacol Exp Ther 315:337-345. (Pubitemid 41380529)
28. Tamai I, Nozawa T, Koshida M, Nezu J, Sai Y, and Tsuji A (2001) Functional characterization of human organic anion transporting polypeptide B (OATP-B) in comparison with liver-specific OATP-C. Pharm Res 18:1262-1269.
29. Tanihara Y, Masuda S, Sato T, Katsura T, Ogawa O, and Inui K (2007) Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters. Biochem Pharmacol 74:359-371.
30. Terada T and Inui K (2008) Physiological and pharmacokinetic roles of H+/organic cation antiporters (MATE/SLC47A). Biochem Pharmacol 75:1689-1696.
31. Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, and Inui K (2001) Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res 18:1528-1534.
32. van Aubel RA, Smeets PH, Peters JG, Bindels RJ, and Russel FG (2002) The MRP4/ABCC4 gene encodes a novel apical organic anion transporter in human kidney proximal tubules: putative efflux pump for urinary cAMP and cGMP. J Am Soc Nephrol 13:595-603.
33. Van Aubel RA, Smeets PH, van den Heuvel JJ, and Russel FG (2005) Human organic anion transporter MRP4 (ABCC4) is an efflux pump for the purine end metabolite urate with multiple allosteric substrate binding sites. Am J Physiol Renal Physiol 288:F327-F333.
34. Zelcer N, Huisman MT, Reid G, Wielinga P, Breedveld P, Kuil A, Knipscheer P, Schellens JH, Schinkel AH, and Borst P (2003) Evidence for two interacting ligand binding sites in human multidrug resistance protein 2 (ATP binding cassette C2). J Biol Chem 278:23538-23544.
35. Zhang H, Cui D, Wang B, Han YH, Balimane P, Yang Z, Sinz M, and Rodrigues AD (2007) Pharmacokinetic drug interactions involving 17alpha-ethinylestradiol: a new look at an old drug. Clin Pharmacokinet 46:133-157.
36. Zhou F and You G (2007) Molecular insights into the structure-function relationship of organic anion transporters OATs. Pharm Res 24:28-36.